Of the myriad of heterocycles known to man, the indole ring stands foremost for its remarkably versatile chemistry, its enormous range of biological activities, and its ubiquity in the terrestrial and marine environments. The indole ring continues to be discovered in natural products and to be employed in man-made pharmaceuticals and other materials. Given the enormous resurgence in indole ring synthesis over the past decade -- highlighted by the power of transition metal catalysis -- this authoritative guide addresses the need for a comprehensive presentation of the myriad of methods for constructing the indole ring, from the ancient to the modern, and from the obscure to the well-known. Following presentation of the classic indole ring syntheses and many newer methods, coverage continues with indole ring syntheses via pyrroles, indolines, oxindoles, isatins, radical and photochemical reactions, aryne cycloadditions. This extensive volume concludes with the modern transition metal-catalyzed indole ring syntheses that utilize copper, palladium, rhodium, gold, ruthenium, platinum, and other metals to fashion the indole ring Indole Ring Synthesis is a comprehensive, authoritative and up-to-date guide to the synthesis of this important heterocycle for organic chemists, pharmaceutical researchers and those interested in the chemistry of natural products.
Autorentext
Professor Gordon Gribble, Department of Chemistry, Dartmouth College, USA
Professor Gribble has been the co-editor of the annual book series Progress in Heterocyclic Chemistry for the past 10 years. His research programs involve several areas of organic chemistry, most of which involve synthesis: biologically active natural products, novel indole chemistry, anticancer triterpenoid synthesis, new synthetic methodology, and novel radical and cycloaddition chemistry of heterocycles.
Inhalt
1 Introduction 1
1.1 Preview 1
1.2 IndoleContaining Natural Products 1
1.3 Biological Activity of Indoles 4
1.4 IndoleContaining Pharmaceuticals 15
1.5 IndoleContaining Materials 21
1.6 IndoleContaining Ligands 28
1.7 Reviews of IndoleRing Synthesis 32
1.7.1 General Reviews on Indole Ring Synthesis 32
1.7.2 Specialized Reviews 32
1.7.3 Name Reactions 33
1.7.4 Miscellaneous Reviews 33
1.7.5 Synthesis of Carbazoles, Carbolines, and Indolocarbazoles 34
1.7.6 Reviews of Indole Analogues 34
References 34
PART I Sigmatropic Rearrangements 39
2 Fischer Indole Synthesis 41
2.1 Preview 41
2.2 Methods 41
2.2.1 Traditional Methods 41
2.2.2 MetalCatalyzed Methods 44
2.2.3 SolidPhase Fischer Indolization Method 56
2.2.4 Other General Methods 57
2.2.5 Hydrazones 63
2.2.6 Other Variations of Fischer Indole Synthesis 66
2.3 Applications of Fischer Indolizations 68
2.3.1 Drug Targets 68
2.3.2 Natural Products 82
2.3.3 Materials 97
2.3.4 General 98
References 108
3 Gassman Indole Synthesis 116
4 Bartoli Indole Synthesis 121
5 Thyagarajan Indole Synthesis 131
6 Julia Indole Synthesis 137
7 Miscellaneous Sigmatropic Rearrangements 139
PART II Nucleophilic Cyclization 145
8 Madelung Indole Synthesis 147
9 WittigMadelung Indole Synthesis 156
10 JonesSchmid Indole Synthesis 165
11 Couture Indole Synthesis 174
12 Wender Indole Synthesis 176
13 Smith Indole Synthesis 181
14 Kihara Indole Synthesis 186
15 Nenitzescu 5Hydroxyindole Synthesis 188
16 EnglerKita Indole Synthesis 206
17 BaileyLiebeskindO'Shea IndolineIndole Synthesis 213
18 Wright Indoline Synthesis 219
19 Saegusa Indole Synthesis 221
20 Ichikawa Indole Synthesis 228
21 Miscellaneous Nucleophilic Cyclizations that Form the Indole Ring 230
22 Sugasawa Indole Synthesis 244
PART III Electrophilic Cyclization 247
23 Bischler Indole Synthesis 249
24 The Nordlander Indole Synthesis 260
25 Nitrene Cyclization 264
26 CadoganSundberg Indole Synthesis 266
27 Sundberg Indole Synthesis 278
28 Hemetsberger Indole Synthesis 287
29 Taber Indole Synthesis 296
30 Knochel Indole Synthesis 299
31 Täuber Carbazole Synthesis 301
32 Quéguiner Azacarbazole Synthesis 304
33 Iwao Indole Synthesis 307
34 Hewson Indole Synthesis 309
35 Magnus Indole Synthesis 310
36 Feldman Indole Synthesis 311
37 Butin Indole Synthesis 313
38 Miscellaneous Electrophilic Cyclizations 317
PART IV Reductive Cyclization 323
39 Nenitzescu o,Dinitrostyrene Reductive Cyclization 325
40 Reissert Indole Synthesis 332
41 LeimgruberBatcho Indole Synthesis 338
42 PschorrHoppe Indole Synthesis 349
43 Mkosza Indole Synthesis 354
44 Rawal Indole Synthesis 361
45 The BaeyerJackson Indole Synthesis and Miscellaneous Reductive Cyclization Indole Syntheses 363
PART V Oxidative Cyclization 381
46 Watanabe Indole Synthesis 383
47 Knölker Carbazole Synthesis 391
48 Miscellaneous Oxidative Cyclizations 396
PART VI Radical Cyclization 403
49 Fukuyama Indole Synthesis 405
50 Other TinMediated Indole Syntheses 409
51 The Murphy Indole Synthesis 412
52 Miscellaneous RadicalPromoted Indole Syntheses 414
53 The GraebeUllmann CarbazoleCarboline Synthesis 424
PART VII Cycloaddition and Electrocyclization 435
54 DielsAlder Cycloaddition ...